DISPERSE DYES FROM 2-HALO-4,6-DINITROANILINE AND SELECTED 2(2'-ALKOXY-5'-ALKANOYL-AMINOANILINO)ALKANES

COLORANTS DISPERSES PRODUITS A PARTIR DE 2-HALO-4,6- DINITROANILINE ET DE CERTAINS 2(2'-ALKOXY-5'-ALCANOYL- AMINOANILINO) ALCANES

English Abstract

DISPERSE DYES FROM 2-HALO-4,6-DINITROANILINE AND
SELECTED 2(2'-ALKOXY-5'-ALKANOYLAMINOANILINO)ALKANES
Abstract of the Disclosure
Disclosed are disperse dyes comprising a chloro- or bromodinitro-
aniline azo moiety and a particular group of 2(2'-alkoxy-5'-alkanoyl-
aminoanilino)alkane couplers. These dyes give exceptional color depth
and brightness, shade permanency on heat setting, build, leveling, barr?
coverage, dye exhaustion and dyeing rate on fibers of polyester, cellulose
acetate, cellulose triacetate, and polyamide (nylon) over widely varying
dyeing conditions of, for example, temperature and pressure. The dyes
exhibit blue shades with excellent colorfastness properties on polyester
fibers and have excellent dyeability by heat fixation (Thermosol) or
exhaust (boil and pressure) methods of application on this substrate.
Uniform dyeability under a wide variety of conditions is an exceptional
feature of the present dyes.
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Claims

I Claim:
1. A compound of the formula
<IMG>
wherein X is bromo or chloro, R1 is straight or branched chain alkyl of 2-10
carbons, and R2 and R3 are each selected from straight or branched alkyl of
3-4 carbons.
2. The compound of Claim 1 wherein R1 is -C4H9.
3. The compound of Claim 2 wherein R2 and R3 are both -CH3.
4. The compound of Claim 1 wherein R1 is -C2H4-?H-C3H7.
5. The compound of Claim 1 wherein R1 is -C6H13.
6. The compound of Claim 1 wherein R1 is -C8H17.
7. The compound of Claim 1 wherein R1 is -C10H21.
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Description

63~1
The present invention concerns disperse dyes comprising a
chloro- or bromodinitroaniline azo moiety and a particular group of
; 2t2'-alkoxy-5'-alkanoylaminoanilino)alkane couplers. These dyes give
exceptional color depth and brightness, shade permanency on heat setting,
build, leveling, barré coverage, dye exhaustion and dyeing rate on poly-
ester fiber over widely diverse dyeing conditions such as temperature,
pressure and dye carrier concentrations. The dyes exhibit blue shades
with excellent colorfastness properties on fibers of polyester, cellulose
acetate, cellulose triacetate, and polyamide (nylon), and have excellent
dyeability by heat fixation or exhaust at boil and pressure on this
, i
substrate. Uniform, level and reproducible dyeability under a wide -~;
vsriety of conditions is a particularly exceptional feature of the
~ present dyes. In addition to the above, the present dyes exhibit excellent
; fastness to light, crocking, wash, sublimation, gas, acid and alkaline
perspiration and p~ stability.
The dyes of this invention are represented by the following
general structure
~02 ~OR2 -~
~ t-~ ~H3 --
~ HNCOR3 ~ -
wherein X is bromo or chloro, P~ is straight or branched chain alkyl of 2-10 `
carbons, and R2 and R3 are each selected from straight or branched alkyl of
1-4 carbons, such as methyl, ethyl, propyl, butyl, and tertiary butyl.
Polyester fibers are difficult to dye with many disperse dyes
at both the boil and under pressure. For dyeing at the boil (atmospheric-
212F.) it is necessary to complicate the process by the addition of
chemical auxiliaries (carriers) to the dyebath to increase the rate of
dyeing and color yield. Pressure dyeing at 220-275F. and thermal fixation
at, fo~ example, 400F. circumvent the use of carriers; however, unless
process pa~amete~s a~e strictly controlled, poor shade reproducibility is
obtained with most disperse dyes. In contrast, even without close con-
trol of application parameters, the dyes of this invention give excellent
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shade reproducibility, excellent build-up, color yield, exhaustion of
dye onto the fiber, dyeing rate, leveling (migration) and barre coverage
o~ polyester fabrics by all of the variou8 dyein~ procedures. These dyes ;;
also bave excellent light, wash, crock, gas, acid or basic perspiration,
and ~ublimation fastness on the above substrate. The dyes exhibit excel- '`
lent pH stability over a range of 4-8 when applied to polyester above the
boil (220-275F,). The build-up characteristics or color yield, exhau~tion
of dye onto the fiber, and rate of dyeing of these dyes are superior to
dyes with almost identical chemical structure. The good reproducibility
of these dyes is reflected in their leveling (migration) and barré coverage ~`
abilities on polyester fabrics. From the above properties these dyes i"
have excellent shade reproducibility by all methods of application (boil,
pressure, heat fixation) on polyester flbers.
Preparation of Cou~ r - The couplers of this invention can be
prepared from either 2-methoxy-5-acetamidoaniline or 2-nitro-4-acetamido-
; anisole and the methyl alkyl ketone with hydrogen and a catalyst. The
preparation for 2-~2'-methoxy-5'-acetamidoanilino)hexane is as follows.
A mixture of 18.0 g. (0.1 mole) of 2-methoxy-6-acetamidoaniline, 100 ml.
of ethanol, 25.0 g. (0.2 mole) methyl n-butyl ketone, and 3.0 g. of 5Z
Pt/carbon is treated at 165C. and 1000 psi. of hydrogen until the uptake ~;~of hydrogen ceases. The solvent and catalysts are removed. ~exane is
added and the solid product is collected by filtration (21.0 g. - 80% yield).
NMR spectroscopy supports the proposed structure.
Dyes - The dyes of this invention shown below are prepared by
diazotization of 2-bromo or chloro-4,6-dinitroaniline and coupling with
one of the above couplers.
EXAMPLE 1
A. Diazotization.
To a solution of nitrosylsulfuric acid obtained from reacting
Na~02 ~18.0 g.) and ~2S04 (125 ml.) is added 1-5 acid (100 ml. of 1 part
propionic acid and 5 parts acetic) below 20C. The system is cooled to
0-5C. and 65.5 grams (0.25 mole) of 2-bromo-4,6-dinitroaniline dissolved
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1!)8631~
in 200 ml. of H2S04 i~ added dropwise below 5C. The reaction is allowed
to stir at 0-5C. for two hours to complete diazotization.
B. Coupling.
To a solution of 26.4 grams (0.1 mole) of 2-(2'-methoxy-5'-
acetamidoan~lino)hexsne in 75 ml. of 1-5 acid is added 250 ml. (0.1 mole~ ~;
~ . ~
~ of the above diazo solution with stirring and below 20~C. The reaction ~ -
,; . ~
is allowed to stand for one hour, p~ured into 800 ml. of water, collected
~- by filtration, washed with water, and air-dried to yield 53.7 grams (98%)
of the following dye.
02N~ N=N--/ \\--NH-CHC4H~
~, ~r HNCOCH3
~ ~ .
~ TABLE l
~2 ~2 '~
\ t/ -N=N--~ / -NH-~H-R
X HNCCR3 .~
Example X ~ R2 R3 ~ ^
2 Cl C4Hg CH3 C 3
3 Br C2H5 CH3
4 Cl C2H5 CH3 C~3
Br CH2-CH(CH3)2 C~3 CH3
6 Br C2H4CH(CH3)2 CH3 Ca3
- 7 Br C2H4-C,HC3H7 CH3
8 Br C6H13 CH3 CH3
9 Br C8H17 CH3 CH3
Cl C10~2l CH3 3
11 Br C4H9 C2H5 C2 5
12 Br C2H5 C * 5 C4Hg
30 13 Cl CH-(CH3~2 C~3 C$3
14 Cl CH2CH(CH3~2 C2H5 3 7
Cl C2~4CH(C~3)2 CH3 2 5 ;

l~B6311
,: :
Althou~h the lnvention h been descrlbed in considerable
detail with particular reference to certain preferred embodiments thereof,
varistions and modifications can be effected within the spirit and scope
of the invention. -
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